Totally regio- and stereoselective behavior of mono- and diactivated cyclic alkenes in the Lu reaction: synthesis of enantiopure functionalized cyclopentanes.
5-Alkoxyfuran-2(5H)-ones and their optically pure 3-p-tolylsulfinyl derivatives, synthetic equivalents of the acyclic esters, react with dipoles generated from allenoates and PPh(3) (Lu reaction), in a completely regioselective, pi-facial selective and endo-selective manner, yielding bicyclic adducts, which are easily converted into optically pure highly substituted cyclopentane derivatives.
García Ruano
José L
JL
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
Núñez
Alberto
A
Martín
M Rosario
MR
Fraile
Alberto
A